First Time Heat

The call had come in pretty late in the week for a Saturday night. I'd had a regular client cancel his Saturday evening spot due to him having the flu, so I just happened to have an opening.

My regular client who was sick was in his mid fifties, divorced, and a wealthy sugar daddy of sorts, but at 29 I was a little too old to figure myself a sugar baby.

This wealthy client liked to buy me little presents and things, though. While that was kind, I didn't really feel comfortable accepting his more expensive gifts that he'd given me in the past. So now he only purchased me little inexpensive items like stockings and body oils. Mostly I liked this client because he was an older, dominant, confident man, a great fuck, and if he could have power fucked me through the mattress and down through the floor I would have gladly let him.

"This will be a new client for you," my boss had told me over the phone.

"Oh?" I asked. I had a pretty decent list of regulars that always requested me when they called in. Usually the younger girls took on the newbies.

"Yes. Everybody else was booked for this Saturday evening. And just so you know, the voice on the phone sounded pretty... young," she said.

I paused a few seconds. "Young? How young?" I asked, a little worriedly.

I was mildly concerned because a different local high-end escort service had gotten into some trouble a little while back because they hadn't been selective enough with their clients. Let's just say the underclassmen of a local high school lacrosse team thought they were going to have a much better evening than they had ended up having, spending the night at the local police precinct.

"No, no! Not that young!" My boss said. "But... young enough," she added.

"We are talking about someone legal?" I asked, just to be sure.

"Yes. Legal, but just barely," she said.

"Is it a first time?" I had asked warily.

I really preferred experienced gentlemen because I liked for them to take the lead in the bedroom and to simply fuck my brains out. I could probably do a first timer but I'd never done one before and it wasn't really what I was used to.

My boss giggled. "It is a first timer. I know you've never done an inexperienced newbie before, but I have faith that you'll do great. So, good luck to you!" She said, and she hung up before I could protest.

Great, I thought. I'll be fucking a man-child on Saturday night instead of my experienced power fucker. I sighed, feeling rather disappointed. This new guy probably wouldn't bring me any gifts, either.

The knowledge that I was going to be showing a newbie the ropes swirled around in my head all Saturday afternoon. I usually liked to meet new clients in a safe place such as a restaurant, and then we'd go on to a nice hotel from there. But this client had assured my boss that the only place he could meet me was at a house. If he was that young he probably couldn't reserve a hotel room anyway.

I got decked out for the date like I normally did. I wore a slinky red sparkly top, a short, tight black leather skirt, and stockings and high heels. I was shaved and waxed as normal and I'd put on some of my favorite perfume. It was called "Dangerous" and it made me feel quite dangerous when I wore it.

Later that evening my Uber dropped me off at a two-story suburban house in a nice neighborhood. The houses around me were one and two-story brick, with decent sized yards. It was a great place to raise a family, probably.

This house had one twenty-ish year old red car parked on the driveway and another equally old white car parked outside on the street. The outside of the house was otherwise dark and quiet but the house had warm-looking lights on the inside that shone out into the dark night.

I double checked the address on the wooden mailbox post and I walked up the driveway and onto the sidewalk that led to the front door. I smoothed down my wavy golden-brown hair and I rang the doorbell.

Several seconds passed and nobody answered, so I rang the doorbell again. I heard arguing on the other side of the door just as it opened.

"Would you calm down? It'll all be alright!" A young male voice said as the door opened.

There stood two individuals just looking at me.

"Hello! I'm Claire," I said.

I looked back and forth from the two "men" who were inside the house. One was tall and pretty nicely built with a shock of short, blonde hair. He grinned at me immediately. The other one was shorter, thinner, with shoulder length straight brown hair and wouldn't look at me for anything. They both were in their stockinged feet.

"Welcome, welcome, Claire! Come on in!" The taller one said. Boy, he was charismatic to a fault. "I'm Chad, by the way," he said.

I was a little confused because I didn't usually do two guys at a time, and I certainly hadn't been warned there would be two men here.

But still I was curious and so I walked inside and Chad closed the door behind me.

"You're Chad?" I said. "I didn't think -" I began, because that was not the name I had been given.

"Yeah, I'm Chad. This here is Oliver," Chad said, pointing to his shorter friend.

I glanced from Chad to Oliver and I smiled widely at the smaller guy.

Oliver was my client.

"Oliver?" I said.

He was looking down at the floor but at his name he glanced up at me and he blushed. "It's nice to meet you," I said.

"Yeah, you too," he said, looking down again at his feet.

"He's real shy," Chad said with an eye roll, being all Mr. Obvious.

I nodded. "I see. But that's okay," I said. "I like shy guys," I lied.

"So... do you just, um, take him upstairs? Or what?" Chad said.

I chuckled. "Well, that's Oliver's decision to make," I said. "Oliver?"

He didn't respond so I decided to take the reins.

"Um... Oliver, what are you drinking?" I asked.

"I just had one of Chad's dad's beers," he offered a little proudly.

I grinned. He was definitely underage for that. "Well, why don't we move on to soda or something like that? Would you want to go into the kitchen first? I'm kind of thirsty," I said.

He flushed again, looking at the wall. "Sure," he said.

But, he didn't move.

Chad finally rolled his eyes. "Come on, Romeo. Let's show her to the kitchen. But I can only hold your hand for so long, you know," he added on a grumble.

Oliver blew out a nervous breath of air and he followed us both into the kitchen.

"Oliver," I said, as he sat down at the table and his friend Chad got three Cokes out of the fridge, "I really like your house," I said.

"Thanks," Chad said. "Actually I live here with my parents. They're on vacation in the Cayman Islands right now," he said.

"Nice!" I said. "How come you didn't go?" I asked.

Chad grinned. "Football practice. Coach would have drawn and quartered me if I had disappeared for two weeks," he said.

"Ugh," Oliver groaned, rubbing his stomach like it hurt.

"And when the cat's away the boys will play?" I asked.

"Something like that," Chad answered with a grin.

"So... where do you guys go to school?" I asked.

"We're both seniors over at Central High. Oliver here just turned eighteen," Chad said. "But I've been eighteen now for a few months," he said, puffing out his chest a little bit.

I grinned. "Aha. I remember being eighteen," I said.

Chad laughed. "Sure! It couldn't have been that long ago for you," he said.

"Um... yeah, let's see... eleven years ago, but thanks," I said with a smile. "What kinds of things do you guys like to do?" I asked Oliver, but Chad answered.

"I play football. And I wrestle," Chad said.

"Nice! Oliver? You?" I asked.

He looked sick. "I have to, um - " and he ran off. I heard a door down the hallway close that I assumed was a bathroom.

"Oh, man. We had tacos earlier for dinner. Maybe that wasn't such a great idea," Chad offered, looking worried.

I smiled. "Poor guy. I'll go check on him. I'll be right back," I said.

I headed down the dark hallway and stopped outside the closed door with the light shining out from the bottom.

"Oliver, are you okay, buddy?" I asked from the outside of the door.

He groaned. "Don't come in! I feel sick. Leave me alone!" He said.

I smiled. "It's okay. Take your time, guy," I said, giving two friendly knocks on the bathroom door.

I came back into the kitchen.

"Is he taking a crap?!" Chad exclaimed in disbelief.

I nodded with a grin.

Chad frowned. "Well, that's gross! And he can't be sick! We only have you for like an hour!" He said. "We can't afford to pay you for any more time!"

I sat back down on a kitchen chair. "Relax. Listen, it's his first time... right?" I asked.

Chad nodded. "Yeah. Poor bastard has never even had a girlfriend. Has never been kissed. I fuck my girlfriend every chance I get. I just wanted him to have the same... you know..."

I waved my hand through the air. "Don't worry about it," I assured him. "I'll make sure Oliver's very happy by the time I leave," I said.

Chad blew out a relieved breath. "Thanks. This took all his Christmas money and some from me for his birthday," he said.

I smiled. "Wow. I think that you're a good friend, Chad."

He beamed.

A few seconds later Oliver came walking slowly into the kitchen.

"Feel better?" I said.

He still had his hand on his stomach. "I don't know," he said.

Chad sent me an alarmed look. He grabbed Oliver and tugged him into the other corner of the kitchen. I pretended not to hear what they were talking about, but words like "man up!" And "don't be a pussy!" Drifted over to me as I sipped my Coke.

I noticed Oliver glancing at me from the corner of my eye. He nodded reluctantly at what Chad was saying.

I turned my head and I looked at Oliver straight on and I smiled at him. I knew that my smile was pretty disarming and I was hoping it would calm his nerves.

"You guys can use my bedroom," Chad said, coming back over to me. "First bedroom at the top of the stairs," he said.

I nodded. "Oliver? Shall we go?" I asked.

I heard Oliver audibly gulp, but he nodded. I stood and held out my hand. "Lead the way," I said.

He stared at my hand for a few seconds.

"Take her hand, dumbass!" Chad said through clenched teeth.

Oliver flushed again. He took my hand in his sweaty palm and led me quickly up the stairs.

Chad's bedroom was indeed the first room at the top of the stairs and it screamed "high school boy". Heavy metal music posters were on the wall along with pro football players and famous pro wrestlers. He had a mirror on one wall with pictures on it of a cute high school girl in a cheerleader outfit which I figured must be his girlfriend. He had some free weights in one corner of his room that I could imagine him using. The bedroom walls were painted dark blue, which complimented the tan carpet nicely. He had a plaid blue bedspread on an unmade queen sized bed with light blue sheets.

I immediately went to the bed and started to make it.

"Do I... um... just take all my clothes off right now?" Oliver asked.

I smiled to myself as I tugged the sheets into place. "Do whatever makes you feel comfortable, Oliver. But we sure don't have to start out triple X rated if you don't want to," I said, glancing over at him.

He waited until I had made the bed, then he loped over and sat down on the comforter.

"This is embarrassing, and it was all Chad's idea. I know I'm going to suck at this," he said, looking down at his long hands with his slender fingers.

"Okay. Stop," I said, sitting on the bed next to him. "Tell me what's worrying you," I said.

He scrunched up his face. "Lots of things. What if I can't come? What if I come too fast? What if I do something embarrassing? What if-"

"Okay," I said, with a gentle chuckle. I put a calming hand on his thigh. "Take a deep breath, Oliver. Here's what we'll do. Let's set some rules at the get-go, okay?"

"Rules? Like what?" He asked dubiously.

"Like... you can come as many times as you want... okay? Don't worry about being too fast or too slow, alright? We both know this isn't a fakey porn shoot. There are no expectations here. You set the rules, got it? If you like what's happening, say so. If you don't like what's happening, say so and we'll change it. Sound good?" I asked.

He blew out a big breath. He looked a little bit more relieved.

Oliver really was a cute, normal-looking, average kid, I thought as I studied him. His friend Chad was probably considered better looking by the girls. Chad had a few pimples on his face but was outgoing as hell so they weren't all that noticeable. It was easy to see why his quiet best friend Oliver got overlooked with Chad around. The smaller kid had no self confidence to speak of. But in direct contrast with Chad, Oliver had beautiful porcelain skin. He had skin that even I envied.

"You know, you're really a cute guy," I blurted out.

He looked up to make sure I wasn't blowing smoke up his ass and then he flushed and smiled.

"And your skin!" I said. "It's absolutely gorgeous!" I said. I reached out and ran a finger down his cheek. His flush intensified.

"Someday, Oliver, you're going to make a girl very, very happy, I just know it," I told him.

He looked away but couldn't hide his half-grin.

"Okay. So what do you want to do first?" I asked. "Let's start easy is my suggestion."

Oliver resembled a deer caught in a pair of bright car headlights. "I don't know," he said, shaking his head.

"Hum," I said. "Well, how about I give you a little backrub?" I suggested. "That will loosen you up a bit," I said.

He hesitantly nodded. "You mean like with essential oils and shit?" He asked.

I laughed. "Nope. Just with my bare hands," I said.

"Oh. Okay. That would probably work," he said.

I climbed behind him on the bed and I put my hands on his shoulders over his gray t-shirt. He felt really tense so I started to massage him. "So, Oliver. Tell me a little bit about yourself. What kinds of things do you like to do for fun?" I asked as my fingers worked.

"Um... well I play a lot of video games. I like geocaching. And I play the saxophone," he said.

"That's cool. But you'll have to tell me, what's geocaching?" I asked.

"Oh. It's when you go to a specific location that you find on a geocaching app. You use coordinates to find the place. Then you usually find a logbook that someone's hidden there and you sign your name on it. It's kind of like a treasure hunt. I do it with my dad or with Chad sometimes," he said.

"Aha! That sounds like fun," I said as I dug my thumb into a particularly stubborn knot on the back of Oliver's neck. "What about your favorite subjects in school?"

"I like anything science, especially space stuff. But I also like band. And I like my shop class. We're making chairs right now," he said.

"Wow, you're really well-rounded, I think. Do you drive?" I asked.

He nodded.

"I've had some really fun experiences in the backseat of cars," I chuckled.

He shrugged. "Man, I have not," he said.

"Do you ever think about it? Taking a special girl wherever kids go to make out?" I asked.

He shrugged and then shook his head. "Nobody would want to go with me," he said.

"Oh, now that's not true!" I said emphatically. "Have you ever asked anyone?"

He just shook his head.

"Hum. Tell me: What kind of fantasies do you have?" I asked him.

He paused, but he shrugged again.

"Well, what do you like to think about when you beat off?" I asked.

He looked back at me in horror.

I chuckled. "Come on. Everybody does it, I guarantee you. What kind of things do you think about?" I asked him in a whisper, my lips in his hair just right next to his ear.

He shuddered from my closeness. "Um... well..."

"Can you tell me? Odds are we can make it happen tonight," I whispered.

"Well, I... I sometimes think about this girl Stacey at school. She's a cheerleader friend of Tanya's, Chad's girlfriend. She has these really full lips. I guess I often think about her lips around my..."

"Gotcha!" I said. "That's a great fantasy!" I added.

"You don't think it's pervy?" He asked.

"What? No! I mean everybody has fantasies. I'd imagine lots of kids at your school star in other kids' fantasies."

He grinned a bit at that. "I guess," he admitted.

"Since you like Stacey's mouth... why don't we make tonight all about lips? Would you like for me to kiss you?" I asked him.

He shrugged. "I've never been kissed. I don't know what I'm doing," he said.

I took my hands off his shoulders and I moved so that I was sitting in front of him. I took his hands in mine.

"Aww, Oliver, kissing is pretty easy. Here," I said, scooting a little bit closer to him. "You just start out like this..." I said. I started to lean in. "Look into the other person's eyes. Move in a little closer... and I'll tilt my head so our noses don't bump..."

Truth be told he looked absolutely terrified, but he managed to pucker his lips a bit and when mine touched his, his lips were soft and trembling.

The knowledge of his sweet nervousness hit me in my chest and then zinged straight down to my pussy. What was happening right now? Kissing this boy's unsure lips was shockingly quite possibly one of the most arousing moments of my life.

I let my lips linger on his until I felt his tongue peek out. I met his tongue with mine and I opened my mouth and then I really kissed him.

He moved right along with me until he suddenly nipped very gently at my bottom lip. It was then my turn to shiver.

I smiled, breathing a bit heavy. "That was wonderful, Oliver," I murmured.

"R-really?" He asked.

I nodded. "Let's do it again," I said.

This time Oliver was a bit more fearless as he kissed me, his young mouth begging for more from me. I extended my tongue and lightly licked his bottom lip. He chuckled and continued the kiss.

It was astounding. It was like I was watching the boy bloom right before my eyes.

I reached my hands up to clasp them behind his neck and he scooted in even closer.

We kissed like that for several minutes, our tongues playing together wildly.

When I finally pulled away he looked a little bit kiss-drunk.

And I felt that way.

"I think you're really getting the hang of kissing!" I praised.

"Yeah?" He asked.

I nodded. "Yeah. How about we lie down on the bed now?" I said.

I kicked my high heeled shoes off and urged him to lie down on his side. I did the same. I leaned in closer and kissed him again, but this time I really allowed myself to get lost in the kiss. When I felt the urge to moan I didn't hold back, and when the kiss ended, his lips were swollen and cherry-frosted.

"God, your moans are going straight to my... you know," he said.

"Your cock?" I suggested.

He nodded.

I grinned. "Why don't we take off your shirt?" I suggested.

Oliver sat up a little and grabbed his T-shirt at the nape of his neck and in one motion tugged it off of his body.

I paused. "God, I really love it when a man takes his shirt off like that," I chuckled, surprised to see him do it that way.

How was this young kid so different than what I usually liked, yet he was somehow pushing all of my buttons?

I leaned in to kiss him again. "Touch me," I begged as I ran my hand over his absolutely hairless chest.

He put his hand on my shoulder and I chuckled. "You can touch me anywhere you like," I said to him. "Not just on my shoulder," I said.

His hand slid down until he was tentatively cupping my breast.

"Congrats! You've made it to second base, Oliver," I teased.

He chuckled. "Looks like it," he agreed.

I sat up and took off my dressy sparkly red tank top. Oliver's very prominent Adam's apple jumped in his throat as he took in my black lacy bra.

He traced the lace along the tops of my cups and my nipples hardened just from that indirect touch.

"Oliver," I whispered. "Can I undo your jeans?" I asked.

He exhaled shakily but nodded. "Yeah."

I slid my hand down his chest to his belly button where a thin line of brown hair began. I unbuttoned his jeans and the zipper lowered when I parted his pants. I reached into his baggy jeans to grasp what was still hidden by his black boxer shorts when I froze.

He noticed immediately.

"What's wrong?" He asked me worriedly. "Did I screw something up?" He asked.

I ran my hand up and down the bulge in his boxers in amazement.

Jesus.

The kid was hung like a rhino!

I shook my head. "Oliver, you naughty boy," I chuckled. "Why didn't you tell me that you're hung like a beast!" I accused him playfully.

His face turned fuchsia. "Oh. That," he said, shrinking a bit away from me.

"Yes, that!" I said, leaning in more towards him so that it was impossible for him to get away.

He was bigger than most of my other clients - even my sugar daddy who was average at best - and this cock was probably still growing since its owner was still so young.

"I didn't think it was... I mean, I knew you'd find out eventually, but... well..." he said.

I chuckled. "You're embarrassed? By this stunning hunk of man meat?" I said. I pushed his jeans down over his hips and I tugged the waistband of his boxers down so his cock could come out properly to play.

And I was right. His cock was hands down one of the biggest I'd ever seen.

"I get teased about it a lot," he mumbled.

"Teased? By who?!" I asked in amazement.

"The guys in my fourth period gym class," he said. "And anybody else who has had gym with me like, ever," he added.

He sucked in a breath when I palmed it. It was warm and pulsing and it was absolutely glorious.

The kid must be a shower, but my God, did he have something to show!

"Oliver," I said, shaking my head. "Knowledge of this has to be all over the school. Why haven't the girls been trying to sneak into your bedroom at all hours of the day and night?!" I asked.

He laughed and scratched the side of his nose. "Well... I don't know," he said. "I guess the rest of me isn't all that exciting or desirable," he said.

I smiled. "Now that's a load of bullcrap. You're a shy guy, I get that. But that doesn't change the fact that you've got the biggest dick at Central High School," I said.

He chuckled a bit nervously.

"I probably shouldn't say this, but you're bigger than all my other clients," I told him.

That got his attention.

"What?!"

"I'm serious, Oliver. You could definitely play with the big boys," I said. "And win. Every time."

And he wanted my lips around this. I grinned just thinking about it. What a challenge. And I was definitely up for it.

"Show me your technique," I said. "How do you masturbate with something so big?" I asked him.

"I can't show you that!" He protested.

"Oliver," I said. "You can't give me the keys to your Lamborghini and not show me where the switch for the windshield wipers is," I said.

He laughed. "I've... never thought about it that way," he said.

I grinned, thinking about the male masturbation porn I'd watched before - and really enjoyed. It was always fascinating to me to see how men handled their own bodies.

"Do you two-fist it?" I asked.

He nodded. "Sometimes. I grease up with hand lotion and I turn my fists in opposite directions as I stroke. That feels pretty amazing," he said.

I worked his boxers and jeans down until they were to his middle thighs. His cock stood up proudly between us.

"I'm afraid my mouth may be somewhat of a disappointment to you since I only have the one," I told him.

He chuckled. "No way. Chad talks about the blow jobs his girlfriend gives him. He says nothing feels better... except for straight up sex," he added.

I stroked him a couple times and he shuddered. He was so ready for this - so eager for my touch.

I pushed on his hip so he rolled to his back. "Get comfortable because I'm going to take this bad boy on," I said.

"Um... before you do... can I maybe see your boobs?" He hesitantly asked.

"Of course!" I said. "You can even take my bra off. Oh, but wait," I mumbled. "My bra is the front closure kind. Oops. I should have worn a more standard bra for you," I said.

He shrugged. "I don't know how to take the other kind off either," he said.

"Then go for it!" I said, pushing my breasts towards him. "There's no better time for you to learn how to undo a front closure bra than right now," I said.

Oliver sat up and grabbed my bra at the clasp between my breasts. After a few seconds of fumbling my bra suddenly parted.

"Hey! You got it!" I said.

He grinned, but I watched his eyes widen at my bouncy D cups.

His shaky hand cupped a globe and it was then my turn to shudder when his thumb rubbed over my nipple.

"Wow," he said, cupping my other breast. "They're a lot heavier than I thought they'd be," he said.

I smiled.

"Can I suck them?" He asked.

"My body is yours, Oliver. Except for anal we can do whatever you like," I said.

He jiggled my boobs and chuckled. "Anal," he scoffed, pink cheeked.

"Oh, I like anal, don't get me wrong. I'm just not not cleaned up for it tonight. I didn't think it was something we'd be getting up to," I said.

He shook his head. "That may be a bit advanced for me," he said.

"Right out of the gate? Maybe," I grinned.

His head dipped towards me and his mouth closed around my nipple. I moaned when he licked and sucked me, and my nipple furiously peaked. "Just so you know, deep sucks feel the best," I said.

"Deep ones?" He clarified.

I nodded. "Oh, yeah! Get the entire nipple in your mouth, along with some of the areola," I said. "That feels just otherworldly."

Oliver licked my nipple again and then sucked on the entire nipple deeply.

"Fuck, yes, just like that!" I gasped, arching my back. "So good!" I held the back of his head close to me so he wouldn't move. He was doing a bang-up job!

Oliver sucked and licked my nipples until they were hard and so unbelievably achey.

"Oliver," I moaned. "Yes! That's just perfect!"

"Yeah?" He asked.

I nodded with a big smile. "Yeah. You've got me all warmed up, that's for sure!" I said.

He grinned.

I started kissing down his neck and collarbones much to his surprise. I licked over his flat little pink nipples and he chuckled as he shuddered.

"Are you ready for my mouth?" I asked him. I took his big dick in hand and gave it a couple strokes.

His eyes widened. "Am I?"

I laughed. "It's up to you, buddy," I said. "I'm ready to get that monster in my mouth, quite honestly," I said.

"Okay," he nodded.

I grinned and kissed further down his chest. When I reached his cock I glanced up at him. "Ready?" I asked him again.

He nodded enthusiastically.

I grasped his cock and I blew a gentle breath of air over his swollen cockhead.

"Ungh!" He grunted.

I kissed up the side of his cock and he let out a little whimper. I grinned and stuck my tongue out. I made sure he was watching as I laid his cock against my tongue. Then I slowly closed my lips around his entire member.

"Oooh!" He gasped.

Then I felt the saliva rush into my mouth. I held his cock on my tongue until my tongue was wet enough to move. Then I licked a few lazy, wet swipes all around his cockhead.

In response, he thrust his hips up hard, almost coming off of the bed. His cock got thrusted into the back of my throat causing me to momentarily gag.

"Oh, shit! I'm so s-sorry!" He exclaimed.

I pulled back quickly and grinned. "I figured that would happen," I chuckled. "You're fine," I reassured him.

I took his cock back into my mouth and I slowly began to fellate him, with a hand slowly stroking the lower half of his cock that wouldn't fit in my mouth.

"F-fucking h-hell!" He whispered. "That's f-fucking fantastic!" He gasped. "Your tongue! Your mouth! It's just... fuck!!"

"Like it?" I asked.

I watched as his eyes rolled back into his head and he nodded.

I couldn't help but smile as I sucked him. It was always fun to have such an enthusiastic partner. Plus I couldn't lie - I was getting somewhat of a rush from being this sweet kid's very first.

"Oh, shit!" He suddenly gasped.

All at once I felt him come, his cock bucking between my lips, his cum spurting on my tongue.

I worked to swallow everything he was giving me and when it was over, his face had turned very pink.

"Jesus, I'm so sorry!" He mumbled. "I didn't... I mean, that snuck up on me so fast -" he said.

I pulled off of his softening cock. "Hey, it's okay, remember?" I said. "This was just orgasm number one. However many you have tonight is totally up to you," I said with a grin. "You taste really good, by the way," I said, wiping my thumb at the corner of my mouth.

He grinned but rolled his eyes.

"Well, what do you want to do now?" I asked him.

He blew out a breath. "How about some... MarioKart?" He said, joking.

"Excellent idea!" I chuckled.

He gave me a strange look.

"You'll need to recharge, so I say let's play!"

I put my bra back on, he pulled up his pants, and we played different video games for a little while.

"Don't shoot me! Don't... don't - no!!!" I squealed, but it was too late. My character was dead. "Shit!" I pouted.

Then there was a firm knock on the bedroom door.

"Are you guys playing video games?!" Chad yelled in disbelief.

Oliver and I both cracked up laughing.

Next I put my top back on and we made our way down to the kitchen. Chad was sitting at the kitchen table with a large pepperoni pizza. Tacos for dinner and now pizza. The kid probably ate all the time, I thought.

"Do you want another Coke?" Oliver asked me. "Some pizza?"

"Sure!" I said. "I can always eat," I said.

"You know, I didn't know video games were a part of sex," Chad said with a smirk.

Oliver punched Chad's bicep as he walked past him to the refrigerator.

"Ow!" Chad joked, grabbing his upper arm.

"Oh, we already had some sex," I said with a chuckle. "And Oliver was awesome," I said.

Oliver's face turned bright red.

"Dude!" Chad said with a huge grin. "So you did?! How was it?!"

Oliver chuckled nervously.

"You don't have to tell him, Oliver," I grinned.

"Aw, man!" Chad complained.

We chatted and ate pizza for several minutes. Afterwards, much to Chad's surprise, Oliver and I moseyed back up to his bedroom.

"Ready for round two?" I asked.

Oliver nodded, licking his lips.

"What's something you've always wanted to do?" I asked him.

"Um... I'd like to eat some... some... can I uh... taste you?" He asked.

I beamed. I absolutely loved an eager face between my thighs. "Oh, I can't wait for that!" I gushed. "Want me to strip for you first?" I asked.

Oliver's eyebrows went up to his hairline. "You can do that?" He asked.

"Of course!" I said.

I gave him a nudge and Oliver sat down on Chad's bed with a slight bounce. I stood next to the bed and very slowly started pulling my red sparkly top up. I played peekaboo with my breasts and eventually took my top off. I tossed it at Oliver who caught it with a big smile.

Next I unzipped my black leather skirt and let it fall slowly down to my ankles. Oliver's eyes just about popped out of his head when I stepped out of it.

"You're wearing a garter belt and stockings?!" He gasped.

I nodded. "I can even leave these on," I said with a wink.

He licked his lips again with a nod.

Next I turned around and unhooked my bra in the front, slipping it off my shoulders. I turned back around with my bra hanging from the crook of one elbow with my fingertips covering my nipples.

I walked towards Oliver and took his hands and put them on my breasts.

"Holy hell," he mumbled.

His hands weren't cold and sweaty anymore. And I leaned in and gave him a sensuous kiss.

I backed away from him and started slipping my lacy black panties down. I turned around to show him my naked ass just as I slipped them under my cheeks. I turned my head to look at him behind me and his gaze was riveted to my every move. I turned back around to slip my panties the rest of the way down and when I had my panties in my hand I tossed them at him. He effortlessly caught them and, to my surprise, brought them right up to his nose.

"Ahh, fuck!" He groaned happily. "If that's what you taste like..." he said.

I nodded.

"Shit!" He squeaked.

I climbed on the bed, my stockings and garter belt now my only clothing. I crawled towards Oliver like an animal hunting its prey. He grinned when I was right in front of him and I kissed him deeply.

He kissed me back enthusiastically and when we finished we both were breathing pretty hard.

"Where do you want me?" I asked him.

"On your back. Legs spread," he whispered.

My only answer was a happy whimper.

Oliver settled in between my legs. He just looked at me. "I've only ever seen naked women in porn," he said, shaking his head. "I can't believe this is real," he said. "I'm expecting to wake up at some point," he said.

I chuckled. "I'm here and I'm real. You're not dreaming, my guy. Now," I said. "Explore me. Taste me. Have a little fun," I said, as I spread my legs even wider for him.

Oliver grinned. "I want to touch you," he said.

I nodded.

Oliver reached out a shy hand and touched my mound. "You're hairless," he said.

I nodded again.

"That's so fucking sexy," he said.

He drew a line with his index finger down the center of my mound until he touched my clit.

"That's it," I encouraged.

He touched my inner lips and then seemed somewhat at a loss for what to do next.

"Touch me right at my entrance. See if I'm slick," I whispered.

He nodded and his finger tentatively wriggled just at my opening. He then pulled his shiny finger back and he smelled it. He blinked a couple times and grinned.

I chuckled.

"Can I taste you now?" He asked.

I nodded. "Please," I said.

Again, this was so different from what I usually experienced. My clients were mostly take-charge kind of guys. They wanted me to be comfortable, sure, but they never asked for my permission. If they wanted to touch me, to take me and fuck me, they just did.

Oliver asking me was... refreshing. And kind of sweet.

He lowered his head and I felt his shy tongue on my clit. He wriggled it around and around, and then he tongued my entrance.

"God, you do taste good!" He said.

He didn't wait for a comment, he just dove right back in.

I watched him then, this bashful boy, as he explored a woman for the first time. His eyes were closed, his breath from his nose was hot on my mound. His tongue wriggled and wriggled.

Eventually he stopped. "There. That was the entire alphabet," he mumbled.

I laughed out loud. "Is that what you were doing?" I asked him. "Tracing the alphabet with your tongue over my clit?" I asked.

He flushed and nodded.

"You know what else feels amazing?" I asked.

He shook his head.

"Take my clit into your mouth and suck it and lick it. That will drive a woman wild," I said.

Oliver nodded. He opened his mouth and my clit was then on his tongue. He closed his lips around it and I let out a sharp inhale.

"Oliver!" I groaned. "Yes! Just like that!" I murmured. I gently grabbed the back of his head and held him to me.

Now we were getting serious.

Oliver hummed and I let out a short squeal of delight. His eyes remained closed as he furiously tongued me.

"Will you come if I keep this up?" He asked.

I sighed quietly. "Probably not, because that's just not how my body is wired. I usually need a vibrator for that," I said.

He looked a little defeated.

"Now don't misunderstand me. What you're doing feels absolutely amazing and you're doing everything right," I said.

"Did you bring your vibrator with you?" He asked.

I nodded.

"Go get it. I want to see you come," he said.

I paused. "You do?"

He nodded. "Yeah, I do," he said.

I grabbed my little vibe from my purse, now thankful I had charged it before I came here. I gave it to Oliver as I settled back down on the bed. I showed him where I liked it and he listened intently to my lesson. When it was time for him to drive, he was doing an excellent job.

"I want to see you come for real. No faking," he said.

I laughed. I had been known to fake it a time or two. I never had to fake it with my sugar daddy because he always demanded I come and he was excellent at spotting a fake orgasm. Other clients of mine weren't as observant. I never came from penetration alone. So if I just spontaneously "came" during intercourse, it for sure was fake.

Oliver evidently wanted to see the real thing too.

"Okay. A real orgasm. Just give me a few minutes here," I said. "You can finger me while you wait," I offered.

"I can?" He asked.

I chuckled. "Yes!"

Oliver slid a single index finger into my heat. His mouth fell open. "That's what a pussy feels like?!" He said excitedly. "It's so much better than what I thought it would be!" He said.

I grinned. "I'm glad you like it," I said.

"Can I do two fingers?" He asked.

I nodded.

Oliver then worked two fingers inside of me. He kissed me while the vibrator worked its magic. My hips rocked onto his fingers when he pushed in and they retreated when he pulled out.

"You seem pretty wet," he said.

I nodded. "It's because a really cute and amazing guy is turning me on," I said.

He laughed as if he didn't believe me. I smiled at him because it was totally true.

Several minutes passed. He watched my body then tense up like a coiled spring. "Oliver!" I gasped. "I'm gonna come!" I said.

He nodded, still watching.

Just then the throbs hit me. I closed my eyes and I came, rippling around Oliver's long and slender fingers.

When I opened my eyes, his mouth was agog.

"That was the sexiest thing I've ever felt or seen," he whispered.

I chuckled. "Kiss me again," I said. I couldn't get enough of his kisses, and he was getting damned good at giving them.

"Want to get that big dick inside of me," I mumbled as we kissed. "Are you ready for that?" I asked him.

He nodded. "I've even got condoms," he said.

"Me too! Glow in the dark ones," I said.

Oliver laughed. "Ok, you win. Let's use one of yours," he said. "They sound cool."

"Want me to put it on you?" I asked him.

He hesitated but then he nodded.

"Good because I have a trick. I can do it with just my mouth," I said.

He laughed.

A minute later I had a rolled up condom between my lips. I took his erect cock and slid my lips down it, unrolling the condom as I went.

"Ta-da!" I said when I was finished. His dick was glowing green in the darkened bedroom.

He clapped. "That was very cool!" He said.

I leaned in and kissed him again. "Now. How do you want me? On my back? Riding you? Doggy?" I asked.

"What would you suggest?" He asked.

I grinned. "There's something about plain ol' missionary style that I just like," I said. "You can control everything that way," I said.

He nodded. "Okay."

"Let's take your clothes the rest of the way off," I said. I tugged his jeans and boxers down and paused when I saw his socks. In the end I tugged those off too.

I got on my back on the bed and a very naked Oliver climbed on top of me.

"Kiss me again, Oliver," I whispered.

He did, and our tongues dueled together, with the sounds of our moans of passion filling the bedroom.

He settled down in between my legs. "Okay, now just aim your cock and go slow. You never want to just ram it in," I said.

"Okay," Oliver said nervously.

He had a little trouble finding my entrance so I reached down and guided his cock to the right place. "Okay. Slowly," I said.

And bless him, he went so slow, being very careful with me. I grabbed his ass and squeezed. His eyes widened at my touch.

Finally he bottomed out.

"I think I'm all in," he said.

I nodded. "Your big cock feels amazing, Oliver," I said.

He nodded. "You feel so warm inside!" He said.

I grinned. "Okay, my guy. Now. Pick whatever speed you like. Slow, medium, or you can even pound me into the mattress. It's all up to you," I said.

Oliver thought for a second. "Let me go slow to start off," he mumbled.

He pulled back slower than I'd ever felt before and he pushed in just as slowly too.

"God!" He whimpered. "It feels... it feels..." He pulled back a little too far and he fell out.

"What -" he said, looking down our bodies.

"You slipped out. No biggie. Line 'er up and start again," I said with a smile.

He did it himself this time and once again I had his huge cock inside of me. He experimented with his hips, pumping in and out, in and out, until he reached a medium rhythm that he liked.

I wrapped my legs around his waist and hung on to his ass as it pumped.

"Ooh!" He whispered. "This feels fucking amazing!" He said.

I looked up into his eyes. "Kiss me again," I begged.

He did, kissing me while he fucked me.

"Oh, Oliver! You're such a fast learner," I said, arching my back underneath him.

He grinned, then leaned down and sucked a nipple into his mouth.

"Ooh!" I gasped in surprise. He tongued my nipples back and forth before he kissed me again.

He started to speed things up a little bit, his thrusts a little faster. "What do you like?" He asked. "Slower? Faster?"

I shook my head. "This isn't about me. It's all about you," I said.

He smiled. "Yeah but isn't sex about not being selfish? And making it good for the other person too?" He asked.

"Normally, yes. But our situation is a little bit different," I said.

He shrugged. "I still want to know what you like," he said again.

I looked deep into his eyes. "What I like?" I asked. "You really want to know?"

He nodded.

"Okay. Well, I like a man to just drill me hard into the mattress. I want to be able to still feel him days after he's fucked me. That's what I like," I said.

"You want to walk funny afterwards, you mean?" He asked me with a smirk.

I nodded in all seriousness. "I want sore muscles. I want a sore pussy. I want a man to really fuck me," I said.

Oliver nodded and sped up some more. His thrusts got more powerful until I was grunting with every one.

"Like this?" He asked, a little breathlessly.

"Oh! Oh! Oh!" I said each time he bottomed out. "Yes! Just like this!" I said.

Oliver stared into my eyes as he fucked me hard - another thing that drove me wild. He breathed harshly out of his nose, his mouth set in a determined grimace. I felt like I was truly getting pounded by a wild beast.

It was utterly perfect.

"Oliver!" I cried. "Yes! Please! Don't stop!"

"I wish I could make you come with just my dick," he said.

I nodded. "It's okay. I just don't. But you can make me come again after you do," I said.

"Oh, hell" he groaned. "I'm getting too close!"

"Slow down if you want. It's okay to take a breather so you can last longer. If not, by all means keep going. Either way, you're doing great!" I said.

He chuckled. "I like all of your positive reinforcement," he said.

I laughed. "Way to go, Oliver! You get an A plus! Do pass go and do collect $100!" I said.

He collapsed onto my chest in fits of laughter. "I didn't know you could laugh during sex," he said, grinning.

I nodded. "Sex is supposed to be fun," I said. "Although sometimes really intense and serious sex is just amazing. It all depends. No two experiences are the same," I said.

Oliver began thrusting again. "I don't want to just be good. I want to be your best," he confessed shyly.

I put my hand on the side of his face and I smiled. "Aww, Oliver. I promise. I will never forget you," I said.

Oliver nodded once. "Think I'm gonna come," he whispered.

"Do it!" I urged.

He made a delightful little squeak and froze above me. Then he gave me three little half-thrusts and a big groan. His breaths were heavy. His chest and face were sweaty. His body smelled wonderful.

Then he collapsed onto my chest for good.

I could feel his heartbeat through his chest - it was beating so fast it was almost fluttering. He raised his head up and looked at me. I smiled up at him.

"That. Was. Amazing," he said.

I nodded. "I'm so glad you're having a good time!" I said. "I am too," I added truthfully.

I showed Oliver how to deal with his used condom and then we just laid on Chad's bed next to one another, our hands slowly roaming.

"Shit," he said, glancing at the clock. "Haven't you stayed longer than you were supposed to?"

I placed my hand on his chest. "Don't worry about it. I'm here to show you the ropes, and I plan to do just that," I said.

Oliver smiled.

We had sex again a little later. This time he had me on my elbows and knees with my ass up, and he took me hard from behind.

"You have one fabulous ass!" He said. He couldn't stop thumbing my little asshole as he fucked me. Even better, he used the vibrator on me as we fucked. Surprisingly, I did eventually come and he got to feel me as I clenched uncontrollably around his massive cock.

"Holy hell!" He said as my pussy squeezed and squeezed him.

Once we'd finished there was another knock on the door.

"Dude! It's getting really late! Should I just sleep on the couch?" Chad asked.

I laughed at that, but Oliver wasn't laughing.

"Stay," he said.

Immediately my laughter stopped. The look on his face was so sweet and earnest that I had to blink to be sure I was seeing and hearing what I was.

I knew getting involved with clients was a bad idea. It was a terrible idea. But... God help me... I couldn't say no.

We climbed under the covers and eventually we both drifted off. Sometime later in the deep dark of the night Oliver rolled over on top of me. "Want you," he mumbled.

"Have me," I whispered back.

When the sun was streaming in through Chad's bedroom windows the next morning I knew I'd overdone it. I'd broken the number one rule - developing feelings for clients was off limits. It was terrible. It was awful. But... I couldn't bring myself to feel all that bad about it.

Oliver stood with me in the front doorway after I'd called my Uber. He couldn't stop kissing me. I couldn't stop touching him.

When it finally was time to part, I watched him as my Uber took me away. Oliver standing in the doorway was burned into my memory - a young man with shoulder-length straight brown hair, shirtless and barefoot in just his yesterday's pair of baggy jeans. He waved at me sadly.

My thoughts were all over the place as I traveled. My ride soon stopped at my apartment. I did the walk of shame in my sparkly red top and black leather skirt. I even had runs in both of my stockings, but I didn't care.

I was alone, but it was like Oliver was still with me. I could smell him on my skin. I could still feel his hands on me. I could remember the feeling of that big cock as it moved inside of me.

My cell phone rang as I was lost in my reverie. It was my boss.

"Good morning," she said. "How did the newbie last night go?" She said.

I smiled. "Oliver. His name was Oliver," I said.

There was shocked silence on the line. Then, "Claire, oh my God! You didn't... you didn't fall for him, did you?" She asked me.

I shook my head. "I don't, um... know," I answered honestly.

But, really, who ended up spending the entire night with a client who hadn't paid for it? That was not normal. Reminiscing about Oliver like I was doing right now was not normal, either. Usually sex for me was just about the sex. But this had somehow been something more.

I never had the urge to contact my regular sugar daddy after our dates. So why was I thinking of somehow contacting Oliver? It was impossible, of course. The chance was nihl that my boss would ever give me his phone number.

Luckily, though, before any meeting happened, my boss had to assign the client to each escort.

"Hey," I said. "If ever Oliver or his friend Chad call in for another date... please give them to me," I said. The thought of one of the younger escorts spending time with Oliver almost made my stomach feel nauseous. Hell, the thought of a particular high school girl with luscious lips spending time with Oliver now made me frown deeply.

"Do you think that's wise? Seeing him again?" My boss asked me after a loaded pause.

I chuckled wryly. "Probably not. But please. Give him to me. Oliver is mine," I said with finality.

I hung up my cell phone. Maybe I'd see Oliver again. I wasn't crazy enough to show up at his band concerts, but maybe our paths would cross at sometime in the future. I could only hope.

Until then my last words I had said to my boss rang in my ears.

Oliver was mine.

********************************

The End